FI906307A0 - Process for the preparation of therapeutically active pyrimidine derivatives - Google Patents
Process for the preparation of therapeutically active pyrimidine derivativesInfo
- Publication number
- FI906307A0 FI906307A0 FI906307A FI906307A FI906307A0 FI 906307 A0 FI906307 A0 FI 906307A0 FI 906307 A FI906307 A FI 906307A FI 906307 A FI906307 A FI 906307A FI 906307 A0 FI906307 A0 FI 906307A0
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- cycloalkyl
- alkenyl
- carbon atoms
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 3
- 230000009286 beneficial effect Effects 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000005702 oxyalkylene group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- JASUSRFZNVUXRL-UHFFFAOYSA-N pyrimidin-1-ium-1-amine Chemical class N[N+]1=CC=CN=C1 JASUSRFZNVUXRL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 1
- 210000001013 sinoatrial node Anatomy 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
This invention concerns novel aminopyrimidinium salts of the formula I: <IMAGE> in which R1 is alkyl, alkenyl, cycloalkyl, phenyl, phenylalkyl or cycloalkyl-alkyl; one of R2 and R6 is a basic group selected from amino, alkylamino, dialkylamino of up to eight carbon atoms, pyrrolidino, piperidino and morpholino; and the other of R2 and R6 is hydrogen, alkyl, alkenyl, alkoxyalkyl, phenyl, phenylalkyl, cycloalkyl or cycloalkyl-alkyl; or both of R2 and R6 are basic groups as mentioned above; and R5 is hydrogen, (1-4C)alkyl or (3-6C)alkenyl; or R2 is a basic group as mentioned above, and R5 and R6 together form alkylene or, together with the appendant carbon atoms of the pyrimidine ring, complete a benzene ring; R4 is hydrogen, alkyl, cycloalkyl-alkyl, alkenyl, alkynyl or phenylalkyl; or R4 is an optionally substitutued alkylene or alkenylene linked to the nitrogen atom of the group Q.A.N-, either of which linking groups may thereby completing a ring including two adjacent carbon atoms of Q, the carbon atoms of A and the adjacent nitrogen atom of the group -A.N-; A is a direct bond to the the group -N(R4)- or is alkylene or oxyalkylene; Q is a pyridyl, furyl, thienyl or phenyl moiety; and Y is a physiologically acceptable anion; but excluding a number of compounds specified hereinafter. The invention also includes certain closely related anhydro-base derivatives which, like the formula I compounds, possess beneficial effects on the cardiovascular system (and in particular beneficial effects modulated via the sino-atrial node). Also included are pharmaceutical compositions containing the formula I compound (or a related anhydro-base) as active ingredient, and processes for the manufacture of the various novel compounds.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898909054A GB8909054D0 (en) | 1989-04-21 | 1989-04-21 | Amino heterocycles |
| GB8909054 | 1989-04-21 | ||
| GB898910548A GB8910548D0 (en) | 1989-05-08 | 1989-05-08 | Heterocyclic compounds |
| GB8910548 | 1989-05-08 | ||
| PCT/GB1990/000595 WO1990012790A1 (en) | 1989-04-21 | 1990-04-19 | Pyrimidine derivatives |
| GB9000595 | 1990-04-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI906307A0 true FI906307A0 (en) | 1990-12-20 |
| FI95377B FI95377B (en) | 1995-10-13 |
| FI95377C FI95377C (en) | 1996-01-25 |
Family
ID=26295250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI906307A FI95377C (en) | 1989-04-21 | 1990-12-20 | Process for the preparation of therapeutically active pyrimidine derivatives |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5223505A (en) |
| EP (1) | EP0422178B1 (en) |
| JP (1) | JP2528218B2 (en) |
| KR (1) | KR920700203A (en) |
| CN (1) | CN1024793C (en) |
| AT (1) | ATE112561T1 (en) |
| AU (1) | AU635260B2 (en) |
| BG (1) | BG93508A (en) |
| CA (1) | CA2014457C (en) |
| DE (1) | DE69013112T2 (en) |
| DK (1) | DK0422178T3 (en) |
| ES (1) | ES2064727T3 (en) |
| FI (1) | FI95377C (en) |
| GB (1) | GB2230527B (en) |
| GR (1) | GR1000371B (en) |
| HR (1) | HRP930793A2 (en) |
| HU (1) | HU209586B (en) |
| IE (1) | IE63502B1 (en) |
| IL (1) | IL94062A (en) |
| MW (1) | MW9090A1 (en) |
| MY (1) | MY105637A (en) |
| NO (1) | NO177054C (en) |
| NZ (1) | NZ233292A (en) |
| PL (2) | PL165917B1 (en) |
| PT (1) | PT93823B (en) |
| RU (1) | RU2108329C1 (en) |
| SI (1) | SI9010799A (en) |
| WO (1) | WO1990012790A1 (en) |
| YU (1) | YU79990A (en) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9012592D0 (en) * | 1990-06-06 | 1990-07-25 | Smithkline Beecham Intercredit | Compounds |
| GB9022644D0 (en) * | 1990-10-18 | 1990-11-28 | Ici Plc | Heterocyclic compounds |
| US5958934A (en) * | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| US5952331A (en) * | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| IL137922A0 (en) | 1998-02-17 | 2001-10-31 | Tularik Inc | Anti-viral pyrimidine derivatives |
| DE69943247D1 (en) | 1998-03-27 | 2011-04-14 | Janssen Pharmaceutica Nv | HIV-inhibiting pyrimidine derivatives |
| DE19851421A1 (en) * | 1998-11-07 | 2000-05-11 | Boehringer Ingelheim Pharma | New pyrimidines, their production and use |
| KR100785360B1 (en) | 1999-09-24 | 2007-12-18 | 얀센 파마슈티카 엔.브이. | Antiviral composition |
| US6410726B1 (en) * | 2000-01-12 | 2002-06-25 | Tularik Inc. | Arylsulfonic acid salts of pyrimidine-based antiviral |
| RU2003135424A (en) * | 2001-05-14 | 2005-05-20 | Бристол-Маерс Сквибб Фарма Компани (Us) | SUBSTITUTED PYRAZINONES, PYRIDINES AND PYRIMIDINES AS LIGANDS OF CORTICOTROPINE RELAXING FACTOR |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| NZ537752A (en) | 2002-07-29 | 2006-12-22 | Rigel Pharmaceuticals Inc | Use of 2,4-pyrimidinediamine compounds in the preparation of medicaments for treating autoimmune diseases |
| US20040242566A1 (en) | 2003-03-25 | 2004-12-02 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| AU2004253967B2 (en) * | 2003-07-03 | 2010-02-18 | Cytovia, Inc. | 4-arylamino-quinazolines as activators of caspases and inducers of apoptosis |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| JP4886511B2 (en) | 2003-07-30 | 2012-02-29 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Method for treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
| CA2535619A1 (en) | 2003-08-13 | 2005-02-24 | Takeda Pharmaceutical Company Limited | 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors |
| JP2007505121A (en) | 2003-09-08 | 2007-03-08 | 武田薬品工業株式会社 | Dipeptidyl peptidase inhibitor |
| GEP20094679B (en) | 2004-03-15 | 2009-05-10 | Takeda Pharmaceuticals Co | Dipeptidyl peptidase inhibitors |
| DK1814878T3 (en) | 2004-11-24 | 2012-05-07 | Rigel Pharmaceuticals Inc | SPIRO-2,4-PYRIMIDINE DIAMINE COMPOUNDS AND APPLICATIONS THEREOF |
| US7872124B2 (en) | 2004-12-21 | 2011-01-18 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| KR101278397B1 (en) | 2005-01-19 | 2013-06-25 | 리겔 파마슈티칼스, 인크. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| CA2604551A1 (en) * | 2005-05-03 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Jak kinase inhibitors and their uses |
| JP5148483B2 (en) | 2005-05-26 | 2013-02-20 | テイボテク・フアーマシユーチカルズ | Process for producing 4-[(1,6-dihydro-6-oxo-2-pyrimidinyl) aminobenzonitrile |
| ME02005B (en) | 2005-09-14 | 2012-08-31 | Takeda Pharmaceuticals Co | Dipeptidyl peptidase inhibitors for treating diabetes |
| CN101360723A (en) | 2005-09-16 | 2009-02-04 | 武田药品工业株式会社 | Process for preparing pyrimidinedione derivatives |
| EP1993612A4 (en) * | 2006-01-31 | 2010-05-05 | Univ Yale | COMPOSITIONS AND METHODS FOR TREATING COGNITIVE DISORDERS |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| CL2008000467A1 (en) | 2007-02-14 | 2008-08-22 | Janssen Pharmaceutica Nv | COMPOUNDS DERIVED FROM 2-AMINOPIRIMIDINE, HISTAMINE RECEIVER MODULATORS H4; YOUR PREPARATION PROCEDURE; PHARMACEUTICAL COMPOSITION THAT INCLUDES SUCH COMPOUNDS; AND ITS USE TO TREAT A SELECTED INFLAMMATORY DISORDER OF ALEGIA, ASMA |
| US20080217501A1 (en) * | 2007-02-14 | 2008-09-11 | Chad Jensen | Power a-frame |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| TWI468407B (en) * | 2008-02-06 | 2015-01-11 | Du Pont | Mesoionic pesticides |
| WO2012135697A2 (en) * | 2011-03-30 | 2012-10-04 | H. Lee Moffitt Cancer Center & Research Institute Inc. | Novel rho kinase inhibitors and methods of use |
| US10172856B2 (en) | 2017-04-06 | 2019-01-08 | Janssen Pharmaceutica Nv | 2,4-diaminopyrimidine derivatives as histamine H4 modulators |
| AU2018352695A1 (en) | 2017-10-19 | 2020-05-28 | Effector Therapeutics, Inc. | Benzimidazole-indole inhibitors of Mnk1 and Mnk2 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB815833A (en) * | 1956-09-26 | 1959-07-01 | Boots Pure Drug Co Ltd | Phenanthridine compounds |
| BE492034A (en) * | 1948-11-05 | |||
| US2784124A (en) * | 1953-07-01 | 1957-03-05 | Howard R Moore | Method of coating ferrous metal surface and composition therefor |
| US2748124A (en) * | 1954-05-06 | 1956-05-29 | Searle & Co | 1-(4-anilino-2-pyrimidino)-3-alkylureas |
| US2845425A (en) * | 1956-10-04 | 1958-07-29 | Lilly Co Eli | Substituted aminopyrimidines |
| DE1241832B (en) * | 1963-02-23 | 1967-06-08 | Hoechst Ag | Process for the preparation of pyrimidinium compounds |
| DE1445740A1 (en) * | 1963-09-04 | 1968-11-28 | Bayer Ag | Process for the preparation of bispyrimidinium compounds |
| GB1229413A (en) * | 1967-06-14 | 1971-04-21 | ||
| IN142539B (en) * | 1974-05-10 | 1977-07-23 | Ciba Geigy India Ltd | |
| US4339453A (en) * | 1979-07-23 | 1982-07-13 | Merck & Co., Inc. | Antimicrobial aminopyrimidinium salts |
| GR80171B (en) * | 1983-08-29 | 1985-01-02 | Ciba Geigy Ag | N-(2-nitrophenyl)-4-aminopyrimidine derivatives process for the preparation thereof and use |
| US4725600A (en) * | 1984-07-13 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent |
| DE3717480A1 (en) * | 1987-05-23 | 1988-12-01 | Shell Agrar Gmbh & Co Kg | Novel herbicidal and microbicidal 2,6-diaminopyrimidines |
| IL88507A (en) * | 1987-12-03 | 1993-02-21 | Smithkline Beckman Intercredit | 2,4-diaminoquinazolines, process for their preparation and pharmaceutical compositions comprising them |
-
1990
- 1990-04-06 IE IE125890A patent/IE63502B1/en not_active IP Right Cessation
- 1990-04-09 GB GB9007964A patent/GB2230527B/en not_active Expired - Fee Related
- 1990-04-11 NZ NZ233292A patent/NZ233292A/en unknown
- 1990-04-11 IL IL9406290A patent/IL94062A/en not_active IP Right Cessation
- 1990-04-12 CA CA002014457A patent/CA2014457C/en not_active Expired - Fee Related
- 1990-04-19 KR KR1019900702652A patent/KR920700203A/en not_active Ceased
- 1990-04-19 DE DE69013112T patent/DE69013112T2/en not_active Expired - Fee Related
- 1990-04-19 EP EP90906289A patent/EP0422178B1/en not_active Expired - Lifetime
- 1990-04-19 YU YU00799/90A patent/YU79990A/en unknown
- 1990-04-19 DK DK90906289.5T patent/DK0422178T3/en active
- 1990-04-19 AU AU54354/90A patent/AU635260B2/en not_active Ceased
- 1990-04-19 AT AT90906289T patent/ATE112561T1/en not_active IP Right Cessation
- 1990-04-19 RU SU4894489A patent/RU2108329C1/en active
- 1990-04-19 ES ES90906289T patent/ES2064727T3/en not_active Expired - Lifetime
- 1990-04-19 HU HU903555A patent/HU209586B/en not_active IP Right Cessation
- 1990-04-19 JP JP2506034A patent/JP2528218B2/en not_active Expired - Lifetime
- 1990-04-19 WO PCT/GB1990/000595 patent/WO1990012790A1/en not_active Ceased
- 1990-04-20 SI SI9010799A patent/SI9010799A/en unknown
- 1990-04-20 PL PL90301231A patent/PL165917B1/en unknown
- 1990-04-20 PL PL90284871A patent/PL165502B1/en unknown
- 1990-04-20 PT PT93823A patent/PT93823B/en not_active IP Right Cessation
- 1990-04-20 US US07/513,304 patent/US5223505A/en not_active Expired - Fee Related
- 1990-04-21 MY MYPI90000670A patent/MY105637A/en unknown
- 1990-04-21 CN CN90103931A patent/CN1024793C/en not_active Expired - Fee Related
- 1990-04-23 GR GR900100304A patent/GR1000371B/en not_active IP Right Cessation
- 1990-12-06 MW MW90/90A patent/MW9090A1/en unknown
- 1990-12-20 NO NO905519A patent/NO177054C/en not_active IP Right Cessation
- 1990-12-20 FI FI906307A patent/FI95377C/en not_active IP Right Cessation
- 1990-12-21 BG BG093508A patent/BG93508A/en unknown
-
1993
- 1993-04-06 HR HRP-799/90A patent/HRP930793A2/en not_active Application Discontinuation
Also Published As
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| Publication | Publication Date | Title |
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Owner name: ZENECA LIMITED |